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Full text of "Preliminary tests of some N-substituted anisamides and esters of anisic acid as insecticides"

LIBRARY 

STATE PLA Decerfoer 1952 



E-852 



United States Department of Agriculture 
Agricultural Research Administration 
Bureau of Entomology and Plant Quarantine 



I 



PHELIMIMARY TESTS OF SOME N-STJBSTITUTED ANISAMIDES AND ESTERS OF AOTSIC 

ACID AS INSECTICIDES 

By G. T. Bottger, A. P. Yerington.and S. I. Gertler, 
Division of Insecticide Investiga-tions 



Forty-three N-substituted anisaraides and esters of anisic acid were 
tested as insecticides in the laboratory of this Bureau at Anaheim, 
Calif,, from February through October 1950. 

The anisamides are represented by the general formula 



CH3O 





II 

C - N. 



R represents either hydrogen or an alkyl group and R-^ an alkyl, aryl 
or substituted ar^''l, or cycloaliphatic group. Two heterocylic compounds 
were included. They were prepared by reacting anisoyl chloride with 
various amines under suitable conditions. 

The esters of anisic acid are represented by the general formula 



CH3O — ^ C - OR 

R represents an alkyl, aryl or substituted aryl, or cycloaliphatic 
group. The esters were prepared by reacting anisoyl chloride with vari- 
ous alcohols or phenols under suitable conditions. The compounds were 
tested against three to five species of insects and one spider mite. 
^The following species were usedj 

Insect Stage 

Alder flea beetle ( Altica ajiibiens (Lec.)) - Fourth instar 
Armyworm ( Pseudaletia unipuncta (Haw.)) - • Third instar 
He'lery leaf tier ( Phlyctaenia 

rubigalis (Cuen. ) )- - - - - ------- Do. 

i^arge milkweed bug ( One ope It us 

^.fa sciatur. (Dall.)) Fourth instar 

PelTaphid ( Macrosiphum pisi (Harris)) - - - Second instar, 2- 

or 3- day- old nymphs 

Two-V)otted spider mite ( Tetranychus 

bir^ulatus Harvey) - - - - - - - Nymphs or adults 

\ 



2 



The armywonn, the celery leaf tier, the large allkweed bu^, and the 
pea aphid were reared in the laboratory; the alder flea beetle and the t«o- 
spotted spider mite were collected in the field. 

In the tests with coleoptej-ous or lepidopterous larrae, 24 were used 
per test; 20 milkweed bugs were used per test; the number of aphids averaged 
56 and the mites 97 per test. The test period was 2 days for the larrae, 1 
to 2 days for the aphids, and 2 to 3 days for the mites. The samples wore 
dusted on foliage, and the foliage was placed in petri disnes with larrae 
of the alder flea beetle, the armywonn, and the celer, leaf tier. Uilkweed 
bugs were placed in 8-cm. crystalliting dishes and dusted. Untreated food 
and water were supplied and the dishes covered with coarse xuslin. The 
pea aphids were dusted either on or removed frooa the plant, and were kept 
during the test period on potted i^indsor beaji plants in cloth-capped glass 
battery jars 7 inches in diameter. The two-spotted spider mites wer« dusted 
while on caetor bean leaves and ware then kept in battery jars. 

The samples were first tested for insecticidal action as dusts. All 
were diluted to 10 percent in pyrophyllite and were in good phj'sical condi- 
tion for dusting. 

Materials causing mortalities of 75 percent or higher as dusts were 
applied as sprays to the leaves of five or more growing plants to deter- 
mine whether they would be too injurious to green foliage for practiced use 
a(-,ainst leaf-eating insects. The sprays contained C.5 percent of the ac- 
tive ingredient euid were applied to both sides of the leaves until tnere 
was run-off. 

The results of tests with three insecticides of known value against 
certain insects, made for ccsnparative purposes, are presented in table 1* 

Two compounds caused greater thaji 74-percent mortality to one or more 
species of insects in dust tests, as shown in table 2. These samples were 
*^ive only against the two-spotted spider mite. 

N, N-diisopropylanisamide was the more effective acaricide, causing 
a 91-percent mortality of the active stages of the two-spotted sp -.te 
when used as a 5-pcrcent dust, and a 66-percent mortality as a 1-. t 
dust* A 5-percent dust of cyolohexyl ami sate killed all the active stages 
of this mite, whereas a 1-percent dust caused no mortality at all. 

N, N-diisopropylanisamide was sprayed on the foliare of bean, chard, 
collard, oom, pepper, squash, and toc.ato, and oyclohoxyl anlsate on the 
foliage of bean, collard, corn, pumpkin, and tomato. N, N-dii sop ropy lania- 
amiie caused severe injury to foliage of bean and moderate injury to that 
of , collard, amd s^ash. No apparent injury to foliage resulted 

frc. . ay applications of cycloh''Tv"' •\n'sate. 

Conpounds tliat killed less than 7b percent of an^' species fed dusted 
foliage are given in table 3. The highest mortalities resulted from the 



- 3 - 

use of 2', S'-dichloroanisanilide, pentachlorophenyl eini sate, and o-bromo- 
phenyl anisate. 

In all tests feeding by the oelery leaf tier and the annywonn was 
much to moderate and by the alder flea beetle moderate to slight. Single 
exceptions were the slight feeding of the annywom and no feeding of the 
alder flea beetle on DDT-treated foliage. 



Table 1. — Effectiveness of three insocticides tested against various species 
of insects fed dusted foliage, to be used as standards for com- 
paring results with new compounds as insecticides 



Compound 
(figures indicate 
percent ) 



Insect 



Foliage 



Average 
deposit 
per square 
centimeter 



Average 
kill after 
2 days 



Lindane 0.125 



Micrograms Percent 



Celery leaf tier Sugar beet 
Large milkweed bug Milkweed (seed) 
Pea aphid Windsor bean 



155 
105 
135 
200 



54 

8li/ 
97^^ 



Parathion 0.025 



Two-spotted spider 
mite 



Castor bean 



217 
230 



83 
952/ 



DDT 0.5 



Alder flea beetle 

Armyworm 

Celery leaf tier 



Alder 
Barley 
Swiss chard 



310 

220 
200 



92 
85 
82 



1/ After 1 day. 
2/ After 3 days. 



- 4 - 



Table 2 . --Compound 8 cfiualng prreater than 74-p«rcent mortalltj of ooe op 
more species of Insects fed dusted foliage 



Compound 
(figures Indicate 
percent ) 


Insect 

, 


ATere^j;© deposit 
per square 
cent imetsr 


Arereg* kill 
after 2 cleya 








Perceat 


Anisemlde , 








N.N-dlisopropyl- 10 


Alder flea beetle 


310 







A-nnyworm 


215 


4 




Celery leaf tier 


250 


8 




L&rp,e milkweed bu^ 


265 


/ 




Pea aphid 


310 


39i/ 




TVo-spotted spider mite 340 


100 






230 


100 


5 


do. 


215 


91 


1 


do. 


265 


66 



Anisic acid, 

cycloheiyl ester 10 



5 
1 



Alder flea beetle 340 

Arinywom 265 

Celery leaf tier 295 

Large milkweed bug 250 

Pea aphid 2?0 

Two-spotted spider siite ci40 

310 

do. 250 

do. 230 



38 

38 

581/ 

looi/ 

85 
100 , 

oS/ 



1/ After 1 day. 
2/ After 3 days. 



- 5 - 



Table 3. — Compounds causing less than 75-percent mortality of any species 
of insect fed dusted foliage 









A V O 1 CtgtJ 




T TlRPfit 




kill after 






centimeter 


2 days 






Micrograms 


Percent 


Anisamide, N-allyl- 


Armywom 


215 







Celery leaf tier 


230 







Large milkweed bug 


265 






Pea aphid 


250 






Two-spotted spider mite 


215 






Anisamide, N-benzyl- 



Anisamide, N-cyclo- 
hexyl- 



Anisaraide, N, N-diethyl- 



Anisamide, N-ethyl- 



Anis amide, N-isobutyl- 



Anisamide, N-i sop ropy 1- 



Armyworm 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mite 

Armyworm 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mite 

Armywonn 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mite 

Armyworm 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mite 

ArmjnTorm 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

TwD-spotted spider mite 

Armyworm 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mite 



280 
280 
250 
230 
280 

265 
280 
265 
230 
280 

250 
250 
200 
310 
200 

265 
265 
230 
265 
310 

230 
250 
215 
185 
280 

230 
295 
230 
310 
265 




4 

10 . 

ol/ 


8 





8 
15 

25 
56 

29 


30 






8 








10 , 

qI/ 





1/ After 1 day. 



. — (Continued) 



C ompound 


Insect 


Average deposit 
per square 
centiaketer 


ATeraj^e 
kill after 
2 days 






- 9 


Pe rcei-t 


Aniseunide, N-methyl- 


Armywomi 
Celery leaf tier 
Largo railfcweed bug 
Pea aphid 

Two-spotted spider mite 


250 
250 
230 
250 
280 


25 


15 , 

oi/ 





Anisamide, N-propyl- 



Arniyworm 

Celery lea:" tier 
Large milkweed bug 

Pea aphid 

Tvro-spotted spider mite 



250 
250 
200 

165 
280 



Anisanilide 



Annyworm 295 

Celery leaf tier 265 

Large milkweed bug 280 

Pea aphid 215 

Digitized'tJf ff^^'i^lte^et Arc^hive 

Anisanilide, 'j'-trur.j- Aray^'orm 26^ 

Celery Ib^ PQI 3 "0 

Large millcweeH bug 250 

Pea aphid 215 

Two-spotted spid»-r mite 230 



Anisanii. • , 2'-chloro- Armywonn 

Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mite 



Aniianilidf?, 3'-c!. 



Inlsanii 



A nnywo rrn 

Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mit;e 

A r...j A rm 

Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mit« 



280 
295 
280 
280 
310 

265 
265 
310 
200 

280 



295 



Si/ 




4 

/ 

oi/ 




17 
10 








5i/ 





http://archive.org/details/paniesaniOOunit 



- 7 - 



Table 3. — (Continued) 



Compound 


Insect 


Average deposit 
per square 
centimeter 


Ave rage 
kill after 
2 days 






Micrograms 


Percent 


AnisEuailide, 2', 5' 
dichloro- 


Armyworm 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

TwD-spotted spider mite 


250 
230 
295 
200 
215 



17 


Anisanilide, 2'-nitro- 


Armyworm 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mite 


280 
250 
265 
230 
230 



4 




Anisanilide, 4'-nitro- 


Armyworm 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mite 


280 
230 
265 
215 
230 



4 

Si/ 




0- An i s sm i s i d i de 


Armyworm 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mite 


280 
265 
250 
215 
200 




4 

20 
01/ 



p-Ani s ani s i di de 


Armyworm 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mite 


295 
265 
250 
250 
280 


k 




Anisic acid, o-bromo- 
phenyl ester 


Annywom 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mite 


265 
230 
230 
250 
310 




H 

44i/ 



Anisic acid, £-bromo- 
phenyl ester 


Armyworm 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mite 


265 
230 
250 
280 
230 




Ih/^ 





2/ After 3 days. 



- 8 - 



Table 3. — (Continued) 







Average deposit 


Are rare 


Conpound 


Insect 


per cquar« 


kill after 






centimeter 


2 days 



Microrra.x8 Percent 



Anisic acid, £-te rt-butyl- Arraywonn 280 

phenyl ester Celer,- leeif tier 510 

Large ndikweed bug 230 

Pea aphid 215 

Two-spotted spider mit« 250 



Anisic acid, o-ohloro- 
phenyl ester 



Anisic acid, o-cyclo- 
hexylphenyl ester 



Armywonn 250 

Celery leaf tier 280 

I«Lrge miilcweed bug 250 

Pea aphid 250 

Two-spotted spider mite 260 

Amyworm 265 

Celery leaf tier 215 

Large milkweed bug 510 

Pea aphid 185 

Two-spotted SDider mite 510 




IS 

%/ 




oi/ 





Anisic acid, 2,4-di- 

chlorophenyl ester 



Armywonn 2 75 

Celery leaf tier 200 

Large milkweed bug 265 

Pea aphid 200 

Two-spotted spider mite 280 







Anisic acid, £-ethyl- 
phenyl ester 



Armyworra 295 

Celery leaf tier 250 

Large milkweed bug 230 

Pea aphid 215 

Two-spotted spider mite 250 



252/ 
Si/ 



Anisic acid, o-nitro- 
phenyl ester 



Anisic ac< d, £-nitro- 
phenyl ester 



Armyworm 250 

Celery leaf tier 265 

Large milkweed bug 215 

Pea aphid 510 

Two-spotted spider mite 510 

Ansyworm SIO 

C«ler>' leaf tier 510 

Large - - 266 

Pea ai 266 

Two- spotted spider mite 216 



8 

17 
















- 9 - 






Table 3. — (Continued; 








W KJUlLf \J \JLXx\JL 


Tn R A r*"!" 


Average deposit 
centimeter 


Ave rage 

Ck. 1.1.x. CIX U6X^ 

2 days 






Micrograms 


Percent 


Anisic acid, phenethyl 
ester 


Annyworm 
Celery leaf tier 
Large milkweed bug 
Pea ftDhi d 

Two-spotted spider mite 


250 
215 
295 
215 
215 





Anisic acid, penta- 
chlorophenyl ester 


Armyworm 
Celery leaf tier 
Large milkweed bug 
Pea anhi d 

Two- spotted spider mite 


250 
295 
230 
250 
295 


73 





oV 




Anisic acid, phenyl 
ester 


Armyworm 
Celery leaf tier 
Large milkweed bug 
Pea anhi d 

Two-spotted spider mite 


230 
250 
250 

265 




24 


Anisic acid, phenyl- 
hydrazide 


Armyworm 
Celery leaf tier 
Large milkweed bug 
Pea anh i d 

Two-spotted spider mite 


230 
250 
230 

PRO 
280 


4 



Si/ 




Anisic acid, m-tolyl 
ester 


Armyworm 
Celery leaf tier 
Large milkweed bug 
Pea anVii d 

Two-spotted spider mite 


295 
250 
265 

265 









Anisic acid, o-tolyl 
ester ~ 


Armyworm 

Celery leaf tier 

Large milkweed bug 

Two-spotted spider mite 


310 
295 
250 

C £70 

340 









Anisic acid, 2,4,6- 
tribrcmophenyl ester 


Celery leaf tier 
Large milkweed bvig 
Pea aphid 

Two-spotted spider mite 


215 
250 
280 
215 


21^ 
q2/ 




3 1262 0«23« 6471 



Table 3. — (Continued) 







Are rage 


deposit 


Arera^e 


Compound 


I naect 


per 8 


q ^ftre 


dll after 






centimeter 


2 days 



Anisic acid, 2,4,6- 

t richlorcr henyl 
ester 


A rmywc nc 
Celery Jeaf tier 
Large millciretd bug 
Pea aphid 

Two— spotted spider mite 


260 

265 

250 

215 
Tin 


r\ 
\J 


m-Anisotoluidide 


Armywo rm 
Celery leaf tier 
Large milicweed bug 
Pea aphid 

Two-spotted spider mite 


265 
230 
250 
230 



u 


o-Anisotoluidide 


ArT"yworm 
Celerj' leaf tier 
Larg« ir.il Irweed bug 
Pea aphid 

Two-spoCted spider mite 


265 
230 
265 
250 




u 


£- Ani 8 1 1 ui d i de 


Am^.'worm 
Celery leeif tier 
Large milkireed bug 
Pea aphid 

Two-spotted spider mite 


2 80 
250 
250 
200 
260 






Morpholine, 4-ani8oyl- 


Armywo nr. 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mite 


295 
215 
230 
280 
340 






Si/ 




Plperldine, l-anisoyl- 


A rm^'worm 
Celery leaf tier 
Large milkweed bug 
Pea aphid 

Two-spotted spider mile 


340 
265 
310 
310 
310 



IS